Benzyl mercaptan → 4-(benzylthio)benzonitrile

HRID 1740830Notes

Reaction equation

HRID 1740830 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([S:8][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 8525724-(benzylthio)benzonitrileYield 68.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 37.2 g of benzylmercaptan, 36.3 g of 4-fluorobenzonitrile and 42 g of potassium carbonate in 700 ml of butan-2-one is held under reflux for 7 hours. The solvent is evaporated in vacuo, the residue is taken up into water and petroleum ether. The crystals formed are filtered off, washed with water and petroleum ether to give 46 g of 4-benzylthiobenzonitrile as crystals with a melting point of 85° C.

Workup

  1. temperatureunder reflux for 7 hours
  2. customThe solvent is evaporated in vacuo
  3. customThe crystals formed
  4. filtrationare filtered off
  5. washwashed with water and petroleum ether

Sources & evidence

ORD record
ord-0667173570314adc81b581cb702241ae
Source dataset
uspto-grants-1999_10
Patent number
US05972950

Reaction notes

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